Currently
pending before this court is Plaintiff Herbert Davis'
Motion to Compel [#159]. Plaintiff seeks an order
from this court compelling the Suffolk County District
Attorney's Office (the “D.A.'s Office”)
to produce six documents responsive to a December 2016
Subpoena. The D.A.'s Office asserts in its Opposition
to Plaintiff's Motion to Compel [“D.A.'s
Opp'n”] [#162] that the documents are protected
under the work product doctrine.[1]

I. Background

In
December 2016, with this court's authorization,
see Elec. Order [#130], Plaintiff issued a subpoena
to the D.A.'s Office seeking documents relating to
confidential informant Darren Sheridan. Mot. Compel 1 [#159].
In addition to producing what it concluded were responsive,
non-privileged materials, the D.A.'s Office also provided
Plaintiff with two privilege logs, on February 21, 2017, and
June 30, 2017. D.A.'s Opp'n, Exs. 1-2 [#162-1,
#162-2]. Plaintiff has challenged the privilege designation
for six of those documents. The six documents pertain to
Commonwealth v. Peete, SUCR2010-10628, and
Commonwealth v. Carter, SUCR2010-10629, two cases
close in time to the events at issue here, and in which
confidential informant Darren Sheridan was involved. Although
the documents are undated, based on counsel's
representations, it appears as though the documents graft
onto the larger chronology of the alleged events as follows:

. On April 22, 2010, Defendant Stephen C.
McManus assisted the Federal Bureau of Investigation in
orchestrating a controlled buy of narcotics from Shawn Peete
and Terry Carter, using Darren Sheridan as a confidential
informant. Mot. for Disc, Ex. 4, at 8 [#123-4]. Sheridan was
provided with $2, 500 of buy money. Id. Although no
exchange of narcotics took place, Peete and Carter took the
buy money from Sheridan. Id. at 8-9. Only $2, 050 of
the buy money was recovered-the remaining $450 was never
found. Id at 9.

.Thereafter, but prior to the issuance
of Peete and Carter 's indictments on June 21, 2010, an
Assistant District Attorney apparently authored the first
document at issue here, an undated, internal memorandum
regarding the Peete and Carter prosecutions, bearing Document
ID Numbers Case A000004-06; CaseA000010-12;
CaseA000033-35; CaseA000311-13.

. In August 2010, Defendants and other law
enforcement officers began investigating a possible firearm
sale by Plaintiff. Mot. for Disc. 3 [#123].

. On September 23, 2010, after Sheridan
identified Plaintiff for a gun and drug transaction, and then
purportedly captured that transaction by video and audio
device, Defendants arrested Plaintiff. First Am. Compl.
¶¶ 3, 14, 17-18 [#108]; Pl.'s Opp'n to
Dist. Attorney's Mot. to Quash 3 [#58]; Pl.'s
Opp'n to Dist. Attorney's Mot. to Quash, Ex. 2, at 3
[#58-2]. The police immediately executed a search warrant,
but $3, 100 of the government's buy money was not found.
Id at 6.

. On January 20, 2011, Assistant District
Attorney Brian Fahy stated at a hearing on a motion to compel
production of the September 23, 2010, videotape that he
wanted to be sure about the cooperating witness's safety
before giving the video out, that he had reviewed the video,
and that he thought he had “either four or five
additional cases that mirror this similar type of an
operation, all with that same officer, Detective McManus from
Boston Police . . . .” Id. at 10:14-24. The
state was ordered to produce the video. First Am. Compl.,
¶ 40 [#108].

.Sometime after Plaintiffs arrest, but
before his release from custody, Assistant District Attorney
Fahy authored the sixth document at issue here, an undated,
internal memorandum to Assistant District Attorney Allison
Callahan regarding the Peete and Carter prosecutions, bearing
Document ID Numbers Case A000421-23.

. After the state court judge viewed the
September 23, 2010, videotape, she immediately reduced
Plaintiffs bail to personal recognizance, and on January 28
2011, Plaintiff was released from jail. First Am. Compl.
¶ 7 [#108].

. On July 19, 2011, Assistant
District Attorney Callahan gave notice of discovery in the
Commonwealth v. Peete, SUCR2010-10628, and
Commonwealth v. Carter, SUCR2010-10629, reporting
that “Darren Sheridan was involved in the investigation
and subsequent indictment of Herbert Davis for the sale of a
firearm (Docket #SUCR2011-10005.) The Commonwealth
subsequently determined that it could not go forward based on
the state of the evidence and difficulty with the
identification of the defendant ...

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